Production at the curie level of no-carrier-added 6-18F-fluoro- l-dopa

Journal of Nuclear Medicine

Volumn 54, Issue 7, 2013, Pages 1154-1161

  Libert, Lionel C ^a   Franci, Xavier ^b   Plenevaux, Alain R ^a   Ooi, Takashi ^c   Maruoka, Keiji ^d   Luxen, André J ^a   Lemaire, Christian F ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b Parc Scientifique du Sart Tilman   (Belgium)

^c NAGOYA UNIVERSITY   (Japan)

^d KYOTO UNIVERSITY   (Japan)

Author keywords

18F FDOPA; 18F fluoride; Enantioselective; Phasetransfer catalysis; SPE

Indexed keywords

2 FLUORO 4,5 DIMETHOXYBENZYL IODIDE F 18; 6 FLUORODOPA F 18; BIPHENYL DERIVATIVE; CARBON; FLUORINE 18; GLYCINE DERIVATIVE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; AUTOMATION; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PHASE TRANSITION; PRIORITY JOURNAL; RADIOCHEMISTRY; REACTION ANALYSIS; RELIABILITY; ROOM TEMPERATURE;

18F-FDOPA; 18F-FLUORIDE; ENANTIOSELECTIVE; PHASE-TRANSFER CATALYSIS; SPE;

DIHYDROXYPHENYLALANINE; ISOTOPE LABELING; RADIOPHARMACEUTICALS;

EID: 84879995281     PISSN: 01615505     EISSN: None     Source Type: Journal    
DOI: 10.2967/jnumed.112.112284     Document Type: Article

References (40)

1. Egerton A, Demjaha A, McGuire P, Mehta MA, Howes OD. The test-retest reliability of 18F-DOPA PET in assessing striatal and extrastriatal presynaptic dopaminergic function. Neuroimage. 2010;50:524-531.
2. Elsinga PH, Hatano K, Ishiwata K. PET tracers for imaging of the dopaminergic system. Curr Med Chem. 2006;13:2139-2153.
3. Garnett ES, Firnau G, Nahmias C. Dopamine visualized in the basal ganglia of living man. Nature. 1983;305:137-138.
4. Minn H, Kauhanen S, Seppanen M, Nuutila P. 18F-FDOPA: a multiple-target molecule. J Nucl Med. 2009;50:1915-1918.
5. Patel NH, Vyas NS, Puri BK, Nijran KS, Al-Nahhas A. Positron emission tomography in schizophrenia: a new perspective. J Nucl Med. 2010;51: 511-520.
6. Kumakura Y, Danielsen EH, Gjedde A, et al. Elevated [18F]FDOPA utilization in the periaqueductal gray and medial nucleus accumbens of patients with early Parkinson's disease. Neuroimage. 2010;49:2933-2939.
7. Gallagher CL, Johnson SC, Bendlin BB, et al. A longitudinal study of motor performance and striatal [18F]fluorodopa uptake in Parkinson's disease. Brain Imaging Behav. 2011;5:203-211.
8. Klein JC, Eggers C, Kalbe E, et al. Neurotransmitter changes in dementia with Lewy bodies and Parkinson disease dementia in vivo. Neurology. 2010;74:885-892.
9. Fiebrich H-B, Jong JR, Kema IP, et al. Total 18F-dopa PET tumour uptake reflects metabolic endocrine tumour activity in patients with a carcinoid tumour. Eur J Nucl Med Mol Imaging. 2011;38:1854-1861.
10. Oldendorf WH. Stereospecificity of blood-brain barrier permeability to amino acids. Am J Physiol. 1973;224:967-969.
11. Namavari M, Bishop A, Satyamurthy N, Bida G, Barrio Jr. Regioselective radiofluorodestannylation with [18F]F2 and [18F]CH3COOF: a high yield synthesis of 6-[18F]fluoro-L-dopa. Int J Rad Appl Instrum A. 1992;43: 989-996.
12. Dolle F, Demphel S, Hinnen F, Fournier D, Vaufrey F, Crouzel C. 6-[18F] fluoro-L-DOPA by radiofluorodestannylation: a short and simple synthesis of a new labeling precursor. J Labelled Comp Radiopharm. 1998;41: 105-114.
13. De Vries EFJ, Luurtsema G, Brüssermann M, Elsinga PH, Vaalburg W. Fully automated synthesis module for the high yield one-pot preparation of 6-[18F] fluoro-L-DOPA. Appl Radiat Isot. 1999;51:389-394.
14. Kao C-HK, Hsu W-L, Xie H-L, Lin M-C, Lan W-C, Chao H-Y. GMP production of [18F]FDOPA and issues concerning its quality analyses as in USP "fluorodopa F 18 injection." Ann Nucl Med. 2011;25:309-316.
15. Forsback S, Eskola O, Haaparanta M, Bergman J, Solin O. Electrophilic synthesis of 6-[18F]fluoro-L-DOPA using post-target produced [18F]F2. Radiochim Acta. 2008;96:845-848.
16. Azad BB, Chirakal R, Schrobilgen GJ. Trifluoromethanesulfonic acid, an alternative solvent medium for the direct electrophilic fluorination of DOPA: new syntheses of 6-[18F]fluoro-L-DOPA and 6-[18F]fluoro-D-DOPA. J Labelled Comp Radiopharm. 2007;50:1236-1242.
17. Lemaire C, Plenevaux A, Cantineau R, Christiaens L, Guillaume M, Comar D. Nucleophilic enantioselective synthesis of 6-[18F]fluoro-L-dopa via two chiral auxiliaries. Appl Radiat Isot. 1993;44:737-744.
18. Lemaire C, Damhaut P, Plenevaux A, Comar D. Enantioselective synthesis of 6-[fluorine-18]-fluoro-L-dopa from no-carrier-added fluorine-18-fluoride. J Nucl Med. 1994;35:1996-2002.
19. Yin D, Zhang L, Tang G, Tang X, Wang Y. Enantioselective synthesis of nocarrier added (NCA) 6-[18F]fluoro-L-dopa. J Radioanal Nucl Chem. 2003;257: 179-185.
20. Krasikova RN, Zaitsev VV, Ametamey SM, et al. Catalytic enantioselective synthesis of 18F-fluorinated a-amino acids under phase-transfer conditions using (s)-NOBIN. Nucl Med Biol. 2004;31:597-603.
21. Lemaire C, Gillet S, Guillouet S, Plenevaux A, Aerts J, Luxen A. Highly enantioselective synthesis of no-carrier-added 6-[18F]fluoro-L-DOPA by chiral phasetransfer alkylation. Eur J Org Chem. 2004;2899-2904.
22. Krasikova RN, Kuznetsova OF, Fedorova OS, et al. Asymmetric synthesis of 6-18F-L-FDOPA using chiral nickel(II) complexes. Radiochemistry. 2007;49: 512-518.
23. Shen B, Ehrlichmann W, Uebele M, Machulla HJ, Reischl G. Automated synthesis of n.c.a. [18F]FDOPA via nucleophilic aromatic substitution with [18F] fluoride. Appl Radiat Isot. 2009;67:1650-1653.
24. Wagner FM, Ermert J, Coenen HH. Three-step, "one-pot" radiosynthesis of 6-fluoro-3,4-dihydroxy-L-phenylalanine by isotopic exchange. J Nucl Med. 2009;50:1724-1729.
25. DiMagno SG, inventor; Nutech Ventures USA, assignee. A process for the preparation of arylfluoride derivatives. U.S. patent US20110313170A1, December 22, 2011.
26. Satyamurthy N, Barrio JR, inventors; University of California, USA, assignee. No-carrier-added nucleophilic [18F]-fluorination of aromatic compounds using phenyliodonium ylides. U.S. patent WO2010117435A2, April 1, 2010.
27. Lemaire C, Libert L, Plenevaux A, Aerts J, Franci X, Luxen A. Fast and reliable method for the preparation of ortho- and para-[18F]fluorobenzyl halide derivatives: key intermediates for the preparation of no-carrier-added PET aromatic radiopharmaceuticals. J Fluor Chem. 2012;138:48-55.
28. Jew S-S, Yoo M-S, Jeong B-S, Park IY, Park H-G. An unusual electronic effect of an aromatic-F in phase-transfer catalysts derived from cinchona-alkaloid. Org Lett. 2002;4:4245-4248.
29. Yoo M-S, Jeong B-S, Lee J-H, Park H-G, Jew S-S. Evidence of the electronic factor for the highly enantioselective catalytic efficiency of Cinchona-derived phase-transfer catalysts. Org Lett. 2005;7:1129-1131.
30. Lygo B, Beaumont DJ. Two highly effective phase-transfer catalysts for the enantioselective synthesis of a-amino acid derivatives. Chimia. 2007;61: 257-262.
31. Wang Y-G, Ueda M, Wang X, Han Z, Maruoka K. Convenient preparation of chiral phase-transfer catalysts with conformationally fixed biphenyl core for catalytic asymmetric synthesis of a-alkyl- and a,a-dialkyl-a-amino acids: application to the short asymmetric synthesis of BIRT-377. Tetrahedron. 2007; 63:6042-6050.
32. Maruoka K. Highly practical amino acid and alkaloid synthesis using designer chiral phase transfer catalysts as high-performance organocatalysts. Chem Rec. 2010;10:254-259.
33. Maruoka K. Design of C2-symmetric chiral phase-transfer catalysts for practical asymmetric synthesis. Chimia. 2007;61:263-268.
34. Lemaire C, Gillet S, Ooi T, et al. Enantioselective synthesis of 2-[18F]fluoro-Ltyrosine by catalytic phase-transfer alkylation. J Labelled Comp Radiopharm. 2001;44(suppl):S857-S859.
35. Ooi T, Maruoka K. Recent advances in asymmetric phase-transfer catalysis. Angew Chem Int Ed Engl. 2007;46:4222-4266.
36. Corey EJ, Xu F, Noe MC. A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions. J Am Chem Soc. 1997;119:12414-12415.
37. Jew S-S, Park H-G. Cinchona-based phase-transfer catalysts for asymmetric synthesis. Chem Commun (Camb). 2009;7090-7103.
38. Han Z, Yamaguchi Y, Kitamura M, Maruoka K. Convenient preparation of highly active phase-transfer catalyst for catalytic asymmetric synthesis of a-alkyl- and a,a-dialkyl-a-amino acids: application to the short asymmetric synthesis of BIRT-377. Tetrahedron Lett. 2005;46:8555-8558.
39. Lemaire C, Guillouet S, Plenevaux A, Brihaye C, Aerts J, Luxen A. The synthesis of 6-[18F]fluoro-L-dopa by chiral catalytic phase-transfer alkylation. J Labelled Comp Radiopharm. 1999;42(suppl 1):S113-S115.
40. Zhang L, Tang G, Yin D, Tang X, Wang Y. Enantioselective synthesis of no-carrier-added (NCA) 6-[18F]fluoro-L-DOPA. Appl Radiat Isot. 2002;57: 145-151.